Chemistry - A European Journal

Cover image for Vol. 16 Issue 21

June 1, 2010

Volume 16, Issue 21

Pages 6121–6395

  1. Cover Picture

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    1. Cover Picture: Analytical Applications of Enzymatic Growth of Quantum Dots (Chem. Eur. J. 21/2010) (page 6121)

      Laura Saa, Ana Virel, Jose Sanchez-Lopez and Valery Pavlov

      Version of Record online: 25 MAY 2010 | DOI: 10.1002/chem.201090099

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      Detection of acetylcholine esterase and alkaline phosphatase was made possible by two analytical assays based on the generation of quantum dots for enzymatic products and are described by V. Pavlov et al. on page 6187 ff. The enzymes induce the formation of H2S, which in the presence of cadmium cations yields CdS quantum dots.

  2. Graphical Abstract

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  3. News

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  4. Communications

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    1. Palladium Catalysis

      Activated Carbon as a Mass-Transfer Additive in Aqueous Organometallic Catalysis (pages 6138–6141)

      Nicolas Kania, Bastien Léger, Sophie Fourmentin, Eric Monflier and Anne Ponchel

      Version of Record online: 30 APR 2010 | DOI: 10.1002/chem.201000085

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      Carbon, on active duty: The addition of activated carbon into the reaction medium appears to be a simple and efficient method to solve mass-transfer limitations in aqueous organometallic catalysis (see figure).

    2. Chemiluminescence

      A Nonenzymatic Chemiluminescent Reaction Enabling Chemiluminescence Resonance Energy Transfer to Quantum Dots (pages 6142–6145)

      Shulin Zhao, Yong Huang, Rongjun Liu, Ming Shi and Yi-Ming Liu

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000478

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      Glowing transfer: An efficient chemiluminescence resonance energy transfer (CRET) between a luminol donor and a quantum dot acceptor was observed for the first time from a nonenzymatic reaction involving luminol–NaBrO–CdTe quantum dots (see figure). This work represents significant progress from the previously reported observation of CRET between a luminol donor and a horseradish peroxidase conjugated quantum dot acceptor from an enzyme-catalyzed chemiluminescence reaction.

    3. Tuning Regioselectivity

      Catalytic Regioselective Control in the Diastereoselective 1,3-Dipolar Cycloaddition Reactions of 1-(1-Alkynyl)cyclopropyl Ketones with Nitrones (pages 6146–6150)

      Yanqing Zhang, Feng Liu and Junliang Zhang

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.200903342

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      The power of the catalyst: The cycloaddition pattern of 1-(1-alkynyl)cyclopropyl ketones 1 with nitrones 2 can be controlled by subtle alterations in the choice of catalyst. From the same two starting materials, two useful heterocyclic compounds can be selectively prepared.

    4. Domino Reactions

      A Novel Iodine-Promoted Tandem Cyclization: An Efficient Synthesis of Substituted 3,4-Diiodoheterocyclic Compounds (pages 6151–6154)

      Ke-Gong Ji, Hai-Tao Zhu, Fang Yang, Xing-Zhong Shu, Shu-Chun Zhao, Xue-Yuan Liu, Ali Shaukat and Yong-Min Liang

      Version of Record online: 26 APR 2010 | DOI: 10.1002/chem.201000518

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      Iodine sets allenes ringing: A novel iodine-promoted tandem cyclization reaction of but-2-yne-1,4-diol and 4-aminobut-2-yn-1-ol derivatives leading to substituted 3,4-diiodoheterocyclic compounds has been developed (see scheme). In this reaction, a trace amount of water is needed. Both the iodine anion and cation generated from I2 are used in the reaction. The resulting iodides can then be used in palladium-catalyzed coupling reactions. The reaction conditions are metal-free, mild, and environmentally friendly.

    5. Natural Products

      One-Pot Synthesis of the Metal-Free AD and BC Fragments of Vitamin B12 (pages 6155–6158)

      Felix H. Zelder, Christian Buchwalder, René M. Oetterli and Roger Alberto

      Version of Record online: 20 APR 2010 | DOI: 10.1002/chem.201000350

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      Demetallation of B12: A one-pot synthesis of the metal-free AD and BC fragments of vitamin B12 that combines photo-oxidative scission with subsequent unprecedented demetallation of the natural product is described (see scheme).

    6. Cluster Compounds

      Diastereoselective Self-Assembly of a Homochiral Europium Triangle from a Bipyoxazoline[BOND]Carboxylate Ligand (pages 6159–6163)

      Gülay Bozoklu, Claire Marchal, Christelle Gateau, Jacques Pécaut, Daniel Imbert and Marinella Mazzanti

      Version of Record online: 26 APR 2010 | DOI: 10.1002/chem.201000572

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      A homochiral triangle: An enantiopure europium triangle selectively self-assembles from a new bipyoxazoline[BOND]carboxylate ligand in a concentration-dependent process (see scheme).

    7. Biological Activity

      Multi-tasking with Single Platform Dendrimers for Targeting Sub-Cellular Microenvironments (pages 6164–6168)

      Rami Hourani, Manasi Jain, Dusica Maysinger and Ashok Kakkar

      Version of Record online: 3 MAY 2010 | DOI: 10.1002/chem.201000241

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      Double trouble! Orthogonally functionalised dendrimers have been constructed by using a versatile approach that is widely applicable for therapeutics and diagnostics by combining imaging agents and therapeutics for synergistic effects. Dendrimers containing a covalently linked dipyrromethene boron difluoride (BODIPY) dye and α-lipoic acid perform complementary biological functions and target intracellular lipid droplets (see figure).

    8. Spin Transitions

      Tuning the Spin States of Two Apical Iron(II) Ions in the Trigonal-Bipyramidal [{FeII(μ-bpt)3}2FeII33-O)]2+ Cations Through the Choice of Anions (pages 6169–6174)

      Xin Bao, Ji-Dong Leng, Zhao-Sha Meng, Zhuojia Lin, Ming-Liang Tong, Masayuki Nihei and Hiroki Oshio

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000526

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      Polynuclear FeIIClusters: A new family of {Fe5} cluster compounds formulated with [{FeII(μ-bpt)3}2FeII33-O)]X2 have been synthesised from the solvothermal reactions of 4-amino-3,5-bis(pyridine-2-yl)-1,2,4-triazole with ferrous salts. The spin states of the two apical iron(II) ions in the cationic pentanuclear {Fe5} clusters can be tuned to give the high-spin states by the [Fe2OCl6]2− anion and the low-spin states by SCN/ClO4/I (see scheme).

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
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    1. Click Chemistry

      Cysteine-Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding (pages 6176–6186)

      Stéphane Le Gac, Erik Schwartz, Matthieu Koepf, Jeroen J. L. M. Cornelissen, Alan E. Rowan and Roeland J. M. Nolte

      Version of Record online: 29 APR 2010 | DOI: 10.1002/chem.200903502

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      A thio-millipede invasion! Helical polyisocyanides containing the alanine– cysteine motif in their side chains have been prepared. The cysteine sulfur atoms are regularly aligned along the polymer axis (see scheme), which provides a unique platform for the scaffolding of various entities by using, for example, the versatile thio-click-chemistry postmodification approach.

    2. Quantum Dots

      Analytical Applications of Enzymatic Growth of Quantum Dots (pages 6187–6192)

      Laura Saa, Ana Virel, Jose Sanchez-Lopez and Valery Pavlov

      Version of Record online: 29 APR 2010 | DOI: 10.1002/chem.200903373

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      Dot products: We have developed two analytical assays for enzymatic activity based on the generation of quantum dots from enzymatic products. These assays were applied to the detection of acetylcholine esterase and alkaline phosphatase. These enzymes induce the formation of H2S, which in the presence of cadmium cations yields CdS quantum dots.

    3. Electron Transfer

      Supramolecular Tetrad of Subphthalocyanine–Triphenylamine–Zinc Porphyrin Coordinated to Fullerene as an “Antenna-Reaction-Center” Mimic: Formation of a Long-Lived Charge-Separated State in Nonpolar Solvent (pages 6193–6202)

      Mohamed E. El-Khouly, Dong Kyu Ju, Kwang-Yol Kay, Francis D'Souza and Shunichi Fukuzumi

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000045

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      Long live the tetrad! Efficient charge separation and a long-lived charge-separated state, in nonpolar toluene, of a self-assembled tetrad formed by axial coordination of a fulleropyrrolidine appended with an imidazole ligand coordinating to the zinc center of subphthalocyanine–triphenylamine–zinc porphyrin was achieved (see picture).

    4. Diruthenium Complexes

      Tuning the Magnetic Moment of [Ru2(DPhF)3(O2CMe)L]+ Complexes (DPhF=N,N′-Diphenylformamidinate): A Theoretical Explanation of the Axial Ligand Influence (pages 6203–6211)

      M. Carmen Barral, David Casanova, Santiago Herrero, Reyes Jiménez-Aparicio, M. Rosario Torres and Francisco A. Urbanos

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200903404

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      Feel the influence! The influence of the axial ligand on the energy of the orbitals that constitute the HOMO level of the unit [Ru2(DPhF)3(O2CMe)(L)]+ was analysed using DFT calculations. The calculations demonstrate that an increase in the π-acceptor character of the ligand L leads to the stabilisation of the low-spin state. Intermediate spin systems are also explained.

    5. Protein–Metal Interactions

      A Doppel α-Helix Peptide Fragment Mimics the Copper(II) Interactions with the Whole Protein (pages 6212–6223)

      Diego La Mendola, Antonio Magrì, Tiziana Campagna, Maria Anna Campitiello, Luca Raiola, Carla Isernia, Örjan Hansson, Raffaele P. Bonomo and Enrico Rizzarelli

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200902405

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      The sum of its parts: The copper(II)-binding features of doppel (hDpl) are driven by an aspartic residue. Analyses show that the hDpl(122–139) peptide fragment (see figure) effectively maintains its helical nature even when excised from full-length hDpl. The EPR spectra of each CuII complex has features that overlap the data for the CuII–hDpl interaction and can thus be used to model these interactions in the hDpl α-3 helix.

    6. Zeolites

      Hierarchical ZSM-5 Zeolites in Shape-Selective Xylene Isomerization: Role of Mesoporosity and Acid Site Speciation (pages 6224–6233)

      Christian Fernandez, Irina Stan, Jean-Pierre Gilson, Karine Thomas, Aurélie Vicente, Adriana Bonilla and Javier Pérez-Ramírez

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.200903426

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      Shaping up: The benefits of hierarchical porous zeolites in shape-selective reactions were demonstrated for the isomerization of o-xylene over mesoporous ZSM-5. The introduction of intracrystalline mesopores and modification of the acid site distribution were tuned to optimize the catalytic performance (see graphs).

    7. C[BOND]H Activation

      Double C[BOND]H Activation of Ethane by Metal-Free SO2.+ Radical Cations (pages 6234–6242)

      Giulia de Petris, Antonella Cartoni, Anna Troiani, Vincenzo Barone, Paola Cimino, Giancarlo Angelini and Ornella Ursini

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200903588

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      Two at once: The SO2.+ radical cation assists an exothermic and effective conversion of ethane to ethylene by double C[BOND]H activation at room temperature. Charge and spin effects are strictly related to geometrical constraints of short-lived intermediates, like the ion–molecule complexes containing the ethyl radical and the ethyl cation, respectively (see figure).

    8. Core–Shell Nanostructures

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      Magnetically Recoverable Core–Shell Nanocomposites with Enhanced Photocatalytic Activity (pages 6243–6250)

      Miaomiao Ye, Qiao Zhang, Yongxing Hu, Jianping Ge, Zhenda Lu, Le He, Zhonglin Chen and Yadong Yin

      Version of Record online: 16 APR 2010 | DOI: 10.1002/chem.200903516

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      Sol–gel and calcination: Core–shell structured Fe3O4/SiO2/TiO2 nanocomposites with enhanced photocatalytic activity that are capable of fast magnetic separation have been successfully synthesized by combining two steps of a sol–gel process with calcination (see figure).

    9. Nanocrystal Catalysis

      Colloidal Noble-Metal and Bimetallic Alloy Nanocrystals: A General Synthetic Method and Their Catalytic Hydrogenation Properties (pages 6251–6256)

      Shuyan Song, Ruixia Liu, Yu Zhang, Jing Feng, Dapeng Liu, Yan Xing, Fengyu Zhao and Hongjie Zhang

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200903279

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      Noble-metal nanocatalyst: A general single-step strategy has been developed for the direct thermal decomposition of noble-metal salts in octadecylamine to synthesize octahedron- and rod-shaped noble-metal aggregate nanocrystals and their alloys without introducing any additive into the system (see figure). The catalytic ability of the nanocrystals has been investigated.

    10. Helium Chemistry

      Stabilization of HHeF by Complexation: Is it a Really Viable Strategy? (pages 6257–6264)

      Maria Giordani, Paola Antoniotti and Felice Grandinetti

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.200903282

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      HHeF: Can it be stabilized? The intrinsically unstable HHeF is probably observable only in solid helium at the highest pressures. Alternatively, it could be trapped in cold matrices, but this requires stabilization by complexation effects. The ligands shown in the dark zone of the graphic definitely stabilize HHeF with respect to H+He+F, but drastically reduce the H[BOND]He[BOND]F bending barrier. Overall, the results cast doubts on the conceivable stabilization of HHeF by complexation.

    11. Total Synthesis

      Cyclic 1,2-Diketones as Core Building Blocks: A Strategy for the Total Synthesis of (−)-Terpestacin (pages 6265–6277)

      Barry M. Trost, Guangbin Dong and Jennifer A. Vance

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200903356

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      A diosphenol strategy: A unique strategy has been developed for the enantioselective total synthesis of (−)-terpestacin based on the unusual reactivity of diosphenols. By multiple usage of the diosphenol α-diketone functionality, twice in the “Pd AAA-Claisen” protocol (AAA=asymmetric allylic alkylation) and once by the employment of its oxidized form, the ene-1,2-dione, stereoselective alkylation of cyclopentane-1,2-diketones could be achieved in a programmatically controlled fashion.

    12. Alkyne–Azide Chemistry

      Experimental Evidence for the Involvement of Dinuclear Alkynylcopper(I) Complexes in Alkyne–Azide Chemistry (pages 6278–6284)

      Benjamin R. Buckley, Sandra E. Dann and Harry Heaney

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.201000447

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      Synthesis and ladders! Dinuclear alkynylcopper(I) complexes are prepared by a robust and simple protocol and function as efficient catalysts in copper-catalysed alkyne–azide cycloaddition reactions (see scheme), as predicted by the Ahlquist–Fokin calculations. We also show that the same copper(I) derivatives are formed during reactions by using the Sharpless–Fokin protocol.

    13. Asymmetric Catalysis

      Asymmetric Catalytic Hydrogenolysis of Aryl[BOND]Halide Bonds in Fused Arene Chromium and Ruthenium Complexes (pages 6285–6299)

      Audrey Mercier, Xavier Urbaneja, Wee Chuan Yeo, Piyali Datta Chaudhuri, Graham R. Cumming, David House, Gérald Bernardinelli and E. Peter Kündig

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.201000011

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      Planar chirality—catalytic desymmetrization: A Pd-catalyzed asymmetric hydrogenolysis reaction gives access to highly enantioenriched planar chiral fused arene chromium and ruthenium complexes. Key elements for the efficiency of the process are the use of a very bulky chiral phosphoramidite ligand, DABCO as a borane trapping reagent, as well as substantial kinetic resolution, which helps to enhance the stereochemical outcome of the reaction.

    14. New Chiral N-Heterocyclic Carbene Ligands in Palladium-Catalyzed α-Arylations of Amides: Conformational Locking through Allylic Strain as a Device for Stereocontrol (pages 6300–6309)

      Yi-Xia Jia, Dmitry Katayev, Gérald Bernardinelli, Thomas M. Seidel and E. Peter Kündig

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000031

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      A1,3-strain to the rescue: New Enders/Herrmann-type chiral N-heterocyclic carbene ligands were developed and applied in asymmetric palladium-catalyzed α-arylations of amides, producing 3-alkyl-3-aryloxindoles with high enantioselectivities (up to 96 %). The ligand aryl location and orientation is fixed by conformational locking that minimizes A1,3-strain and enables optimal transfer of chiral information.

    15. Asymmetric Induction

      Transition States and Origins of 1,4-Asymmetric Induction in Alkylations of 2,2,6-Trialkylpiperidine Enamines (pages 6310–6316)

      Joann M. Um, Naeem S. Kaka, David M. Hodgson and K. N. Houk

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000046

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      The origins of asymmetric induction in the intermolecular alkylation reaction of piperidine-based enamines (see scheme) were investigated and described by using density functional theory.

    16. Quaternization

      Stereodivergent Quaternization of 2-Alkyl-2-p-tolylsulfinylacetonitriles: NMR Spectroscopic Evidence of Planar and Pyramidal Benzylic Carbanions (pages 6317–6325)

      José Luis García Ruano, Ana M. Martín-Castro, Francisco Tato, Esther Torrente and Ana M. Poveda

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200903521

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      Remote stereocontrol: Enantiomerically enriched α,α-disubstituted phenylacetonitriles were prepared by stereoselective quaternization of 2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles with different alkyl halides in the presence of bases (see scheme). The stereochemical course of the reactions has been rationalized and supported by NMR spectroscopic studies.

    17. Columnar Mesophases

      Counterion Effects on the Columnar Mesophases of Triphenylene-Substituted [18]Crown-6 Ethers: Is Flatter Better? (pages 6326–6337)

      Martin Kaller, Christopher Deck, Annette Meister, Gerd Hause, Angelika Baro and Sabine Laschat

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000155

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      Is flatter better? Triphenylene-substituted dibenzo[18]crown-6 ethers and their complexes form Colr mesophases with c2 mm, p2 mg or, in the case of X=SCN, p2 gg symmetry in the unit cell (see graphic). With respect to mesophase stabilities, the counterion plays a decisive role rather than the flat and extended aromatic core.

    18. Natural Products

      Immunosuppressive Resveratrol Aneuploids from Hopea chinensis (pages 6338–6345)

      Hui Ming Ge, Wen Hao Yang, Yan Shen, Nan Jiang, Zhi Kai Guo, Qiong Luo, Qiang Xu, Jing Ma and Ren Xiang Tan

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.201000230

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      Two resveratrol aneuploids, hopeachinols A (1) and B (2), and a potent immunosuppressive polyphenol diptoindonesin G (3) were characterized from Hopea chinensis. The structures were elucidated by comprehensive spectroscopic analysis and computational quantum-chemical methods. The distinct structure and immunosuppressive profile of 3 recommended it as a good starting molecule for relevant drug discovery.

    19. Dyes/Pigments

      Synthesis of Symmetrical Multichromophoric Bodipy Dyes and Their Facile Transformation into Energy Transfer Cassettes (pages 6346–6351)

      O. Altan Bozdemir, Yusuf Cakmak, Fazli Sozmen, Tugba Ozdemir, Aleksander Siemiarczuk and Engin U. Akkaya

      Version of Record online: 16 APR 2010 | DOI: 10.1002/chem.200903449

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      One step to energy-transfer cassettes: Symmetrical multichromophoric boron–dipyrromethene (Bodipy) dyes were converted into efficient energy-transfer cassettes in one step. The resulting cassettes have large extinction coefficient antenna modules and Stokes shifts.

    20. Porous Materials

      Reversible Coordination of Dioxygen by Tripodal Tetraamine Copper Complexes Incorporated in a Porous Silica Framework (pages 6352–6364)

      Clément Suspène, Stéphane Brandès and Roger Guilard

      Version of Record online: 16 APR 2010 | DOI: 10.1002/chem.200903148

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      O2or not to O2: A silylated tetraethoxysilated tripodal tetraamine (TREN)-based copper(II) complex has been incorporated in a microporous silica matrix under micellar conditions and by using a double templating method. After surfactant removal by acidic washings and re-metalation with copper(II), the material was shown to reversibly bind O2 with high selectivity (see picture) versus N2 and CO, thanks to the confinement of the copper complexes within the short-range lamellar framework.

    21. Oligomerization

      Oligomerization of 1,2-Ethanedithiol: An Expedient Approach to Oligothiaethylenethioglycols (pages 6365–6373)

      Dvora Berkovich-Berger, N. Gabriel Lemcoff, Sarah Abramson, Mikhail Grabarnik, Sarah Weinman and Benzion Fuchs

      Version of Record online: 21 APR 2010 | DOI: 10.1002/chem.200903397

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      Any H(SCH2CH2)nSH, anytime: A remarkable alkali carbonate induced self-condensation of ethylenedithioglycol (ETG) provides the oligomers: di- (DETG), tri- (TrETG), tetra- (TETG), pentathiaethylenethioglycol (PETG), and so on (see image) without hazardous byproducts. The most efficient carbonate was K2CO3, both in organic and in aqueous media.

    22. Hydrogen-Bond Effects

      Amido-3-hydroxypyridin-4-ones as Iron(III) Ligands (pages 6374–6381)

      Sirivipa Piyamongkol, Yong M. Ma, Xiao L. Kong, Zu D. Liu, Mutlu D. Aytemir, Dick van der Helm and Robert C. Hider

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.200902455

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      Hydrogen-bond effects: Crystal structures of 1-unsubstituted and 1-methyl-substituted pyridinone (see figure) demonstrate that the amido group is almost perpendicular to the pyridine plane in the latter structure and planar for the former structure in which a strong hydrogen bond exists between the 2 and 3 positions. The presence of this hydrogen bond was found to dramatically influence the physicochemical properties of the molecule.

    23. Tandem β-Boration/Arylation

      Tandem β-Boration/Arylation of α,β-Unsaturated Carbonyl Compounds by Using a Single Palladium Complex To Catalyse Both Steps (pages 6382–6390)

      Amadeu Bonet, Henrik Gulyás, Igor O. Koshevoy, Francisco Estevan, Mercedes Sanaú, M. Angeles Úbeda and Elena Fernández

      Version of Record online: 15 APR 2010 | DOI: 10.1002/chem.200903095

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      Dual-action catalysts: Stable dimeric palladium complexes with diphenyl(3-methyl-2-indolyl)phosphine in a P,N-bridging coordination mode have been synthesised in high yield. These compounds showed high activity and selectivity in the catalytic β-boration of α,β-unsaturated esters, ketones, aldehydes and amides (see scheme).

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    3. Graphical Abstract
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    1. You have free access to this content
      Preview: Chem. Eur. J. 22/2010 (page 6395)

      Version of Record online: 25 MAY 2010 | DOI: 10.1002/chem.201090102

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